Notes From The Dark Side: A New Blog by Republican Operative Roger Stone


If the New York Times is going to have Republican columnists we figure The Rumpus should too. So we invited Roger Stone, the architect of the Brooks Brothers Riot (which handed George Bush the presidency) to set up shop on our virtual pages. He was going to write an introduction but he wrote The 10 Best – and Worst – Dressed People of 2008 first. Stone is consumed with money and fashion, things The Rumpus, which is often published using our neighbors stolen wi-fi, doesn’t really understand.

Anyway, we’re moving too fast for introductions. We’ll have an introduction down the road. In the meantime, if you want to know more about Roger Stone check out this profile in the New Yorker by Jeffrey Toobin. – SE


The 10 Best – and Worst – Dressed People of 2008, by Roger Stone

Every year, Hollywood designer and arbiter of fashion, Mr. Richard Blackwell, would publish a list of the ten best and worst dressed people in the demimonde. Mr. Blackwell has since gone to his maker, but the STONEzone refuses to let this fine tradition die. Therefore, the Zone has compiled its official list of the best and worst dressed men and women of 2008. However, first a word regarding the sorry state of fashion in America, and the very few who can plausibly claim to be true possessors of style.

If you want to find the best dressed men in America, you must go into the nation’s statehouses where the lobbyists and titans of special interests sport impeccable suits with classic, refined, and conservative styling. The starchy lawyers aside, lobbyists are the only elegant men left in America. They veritably live night and day in their suits, which is fundamental to the art of looking good in one.

If you want to find the worst dressed men in America, any corner bar should suffice. There you will find men unabashedly wearing baseball hats and tank tops, ill-fitting pants, and blindingly white sneakers. The average American male is an utter disgrace to male sartorial tradition. The ubiquitous gangsta fashion craze alone is enough to nauseate any person of even minimal taste, but the Ashton Kutcher trucker hat craze truly moved American men to the bottom of the fashion rung. To wear a hat indoors, especially a baseball hat, is a veritable fashion felony. It advertises not only bad manners but also poor taste. Ladies, my condolences.

While a true expression of the gold standard in mens personal style, sprezzatura informs the success of the best-dressed woman as well, if to a lesser degree. That’s because men dress, but women dress up. And we like it that way. So for the ladies, wearing an air of effortlessness is just as important as for the men. But a little affectation–even daring–is not only forgivable in woman’s dress, it is often roundly encouraged. Everything else matters in just the same way it does for men–fabric, cut, shape and style. The woman who understands how to wear great clothes naturally is always the best-dressed person in the room.

A list of best-dressed women written by a man is bound to bear the watermarks of an age-old truth about the male worldview: A woman’s clothing is a kind of mental foreplay for men. Being dressed is what comes before being undressed, which is always a pleasure to think about. Just by way of explaining some of the notables on the list below.

The problem of course is that most men just don’t care and don’t care to learn.


In 1528, Baldassare Castiglione in The Book of the Courtier coined the term “sprezzatura.” He wrote,

Avoid affectation in every way possible . . . practice in all things a certain Sprezzatura, so as to conceal all art and make whatever is done or said appear to be without effort and almost without any thought about it.

Therefore, the key is not a closet full of expensive clothing, but rather to look like you haven’t thought about what to wear, even though you look great. A look must never be studied or too precise; it should be nonchalant, even insouciant. Gary Cooper had it. So did Sir Anthony Eden, Douglas Fairbanks, Jr., John Davis Lodge, Cary Grant, and Ambassador Henry Catto.

Sifting through those in sports, academia, politics, government, entertainment, and media, it’s hard to find people who are truly well-dressed as opposed to those whom a wardrobe producer merely outfits. Fred Astaire didn’t just look good in his movies- he looked good all the time. Contrast Astaire with Jeremy Piven of Entourage. I suspect his “Ari Gold” look is not his taste but that of a costumer. Piven at leisure seems slovenly.

The rules are simple, yet few men follow them. The elements of dress must exude confidence in one’s choices. Poor grooming must not detract from your appearance; gentlemen shave those pornstaches. Match your suit to both your body type and age. Find a top-notch tailor and use him (or her). Learn about fabric and choose only those of top quality and appropriate weight for your climate. Trousers should hang from the waist and have a proper break. A suit without cuffs is appropriate, only if you are a gigolo or in a show band. No over sized jewelry of any kind, particularly cuff-links. Match patterns carefully. Black suits are only for chauffeurs and funeral directors. Buy only shoes of the highest quality leather or suede and leave the sneakers in the gym. Lastly, learn to like looking good.

That said, here they are.


Not stylish, but perfectly consistent. His long, lean frame could plausibly sport even a grocery bag. He is also bringing back the idea of going to work in a uniform, like Geoffrey Beene and his daily smock that I always loved.

The dandy of the supply-siders, CNBC host combines old world preppy and classic English-inspired tailoring for a look that is elegant, knowing, and always appropriate. Kudlow’s tie and shirt combinations never miss.

Ignore his Gangsta garb because when Mr. Carter dresses, the cut of his suit and the fit of his collar are always correct. He isn’t afraid of bold stripes. He shines when coupled with Beyonce, but then – who wouldn’t?

Reverend Al has abandoned the Adidas track suits and gold chains of the street radical for more somber three piece suits of a civil rights leader. His lapeled vests are the sign of custom tailoring and good taste. He reinvented himself and outfitted himself accordingly.

John Warner is Old School. Even before he married Liz Taylor, he used the best tailors in New York and London. He still wears the lower right button open on his drape-style double-breasted suits. Has an annoying habit of mixing rep stripe ties with dressier suits…and getting away with it.

Anderson and Sheppard of Savile Row ( make Calvin Klein’s monochromatic suits and sports coats, which he teams with tee shirts or long sleeve polo shirts from his line, a look that is spare, clean and ideal for a designer. The suit or jacket dresses it up, the tee shirt dresses it down.

Ambassador Richard Burt was America’s man in Berlin, but his look is an American twist on European style. Proper and understated, his well-cut suits perfectly match the subtly striped shirts and pin-dot ties. His trousers are creased as if with a knife and his ancient shoes gleam with a well-kept patina.

Ken Aretsky turned the 21 Club around and then bolted off to do “the” East Side New York steakhouse, Patroon, where he has held court for many years. Dapper as the front man in Oren and Aretsky, a fabled spot where politicians, gangsters, sports figures and the high powered rubbed elbows in the 70s, his sartorial tastes haven’t left him. He is impeccable at the door, starched and prosperous looking in his easy-shouldered suits by his pal Alan Flusser. (

Former NFL tight end turned commentator Shannon Sharpe is a tall man, a fact he takes into consideration in his choice to wear a three button suit buttoned at the second button but rolled to the top. It gives his athletic torso a balanced look. His collar is appropriately long for his angular face and his neckwear never distracts.

Although I’d rather see him in stripes, as both governor and attorney general, the Sheriff of Wall Street’s crisp white shirts and Hermes ties stood out as both rich and tasteful. It looked as if he wouldn’t sweat even when Hank Greenberg and Ken Langone got off. The knee-length black socks I cannot explain.


Her clothes are always perfect on her, and she’s never overdone. More important, though, she glows with a mysterious freshly satisfied look. Her husband is indeed a lucky man.

Rihanna dresses so that you cannot take your eyes off of her. She dresses up, she dresses funky, she dresses sexy, she dresses tomboy. In short, she’s redefining pop style. I don’t mind that flawless skin and exquisite self-confidence either.

Fran wears mens tailored English custom suits and shirts with bespoke shoes. It’s mannish yet perfect. On her, the look is real. On Tom Wolfe, it looks like he’s a cross-dressing character in a lesser Dickens novel.

Betancourt proves that freedom really is a beautiful thing.

She pulls off former-slut-who-got-rich-and-cleaned-up-her-act better than anybody(ahem, Madonna). I don’t want to know her, but I wouldn’t mind knowing what’s in her handbag. If her husband dressed consistently in a suit, in which he looks incredible, he would have made the top 10 Men’s list.

A little too skinny for my taste, and I’d prefer that she quit crapping on America, but she rolls the rags right.

There’s a sleek indifference to her presentation that’s wildly attractive. Clothes, no clothes, she looks like she couldn’t care less either way. Plus, the threads go with the tatts and the tat goes with the threads. That’s not an easy trick to pull off, I happen to know.

Makes my best-dressed list anytime, anywhere. Whether she’s wearing one of those grubby barefoot peasant getups from her post-war movie days or Italian couture, she is absolutely the definition of a woman who is guaranteed to get your undivided attention.

La Loren redux. I like her in jeans and a white tee shirt. I like her in Valentino. She just makes everything better–movies, clothes–by being in them.

Come on. Who’s gotten more fashion traction from a mere $150,000 of someone else’s money than the Governor of the great state of Alaska? She went from Alaskan Housewife to Catwalk Candidate overnight.


To have a Brit appear on this list is as near a fashion tragedy as I can imagine. Thin shawl lapels on a pinstripe suit is an abomination. Does the man own a necktie? He wears his trousers far too tight in the seat and haunches. And the man boob-tight tee shirt incident should be enough to expel him from England.

Justin Timberlake takes pop star license with his wardrobe and it does not work. He commits the faux pas of wearing the vest of a three piece suit that is too short so that his shirt and belt may hang out. It’s not cool. It’s slobbish.

Who dresses this guy? Demi? Formal without a necktie, always dressed wrong for the occasion, and the ubiquitous tractor hat? Anyone who accessorizes with a mesh trucker cap ought to be run over by a semi.

Johnny Knoxville dresses so slovenly that one may fairly describe him as a true fashion jackass.

Peter Wentz is sprezzatura gone all wrong. He looks as if he called a costume shop and requested the generic rock star outfit, and his different color stove pipe pants are truly horrific. He is not cool; he is disheveled.

Just an atrocious stew, a walking scrapbook of bad ideas. Great voice, though.

Hooded sweatshirts and sneakers on a grown woman who knows how to talk dirty, well, that’s just a crying shame.

It’s not just me who’s sick of her look; I think she’s sick of herself. How else to explain the outfit she wore to a Gucci benefit this year, which in a civil society would have gotten her 20-to-life.

Look, there’s nothing wrong with looking like a boy. Just try to look like a cute boy, please. Katie Holmes, Agnes Deyn, or sapphic sister Ingrid Cesares might have some pointers. An occasional bath doesn’t hurt either. Fran Leibowitz looks cool, Samron looks butch.

I keep waiting for her to become as good-looking and well-dressed as she is smart. I think, though, she just may have spent too much time living with the livestock in the Afghan countryside.

Which part of “over” does Ivana not understand about the 1970’s? Big shoulders, big hair, pastel colors and ‘power suits”. If she is going to keep chasing Italian Playboys half her age, she is going to have to dress younger.

As the original Ms. once said, “A woman without a man is like a fish without a bicycle.” I might suggest a corollary: “A contemporary woman without a care for her presentation should quit worrying about fish and bicycles and get herself a hairbrush, some good red lipstick (Chanel’s “Fire” never fails), and a highly skilled stylist who can make her look a little less like a disheveled monolith and more like the elegant woman of historic and cultural stature she really is–somewhere deep inside.” P.S. Sorry, but trading in your 70s aviator specs for frameless Palinesque wannabes just isn’t enough. I wanted to do you in the 70’s. Today.

With this first installment the STONEzone will release a list of the 10 Best and Worst Dressed People of the year at the end of every year in the tradition of Mr. Blackwell and my late friend, Eleanor Lambert. HAPPY NEW YEAR


See Also: The Political Animal from The Weekly Standard (pdf download)

See Also: The Dirty Trickster, the New Yorker Profile of Roger Stone

See Also: Bitch Craft, by Bitchy Jones

See Also: Rumpus Resolutions